63082-55-3Relevant academic research and scientific papers
Pd(0)-catalyzed allylic alkylation/Heck coupling in domino sequence
Poli, Giovanni,Giambastiani, Giuliano,Pacini, Barbara
, p. 5179 - 5182 (2001)
A new molecular queuing process has been achieved, in which a single Pd-based catalytic system promotes two unrelated, sequential catalytic cycles in chronologically distinct order. This study demonstrates also that allylic alkylations can be catalyzed by the Herrmann's phosphapalladacycle, a result that further supports the involvement of a Pd(0) species in its mechanism of action.
Asymmetric synthesis of 3,4,5,6-tetrasubstituted piperidin-2-ones by three-component coupling
Davies, Stephen G.,Smith, Andrew D.,Cowley, Andrew R.
, p. 1957 - 1960 (2004)
The asymmetric three-component coupling of α,β-unsaturated esters and alkylidene malonates initiated with a homochiral lithium amide proceeds with high levels of diastereoselectivity, with hydrogenation of the resultant α-substituted β-amino acid derivatives giving a range of differentially protected 3,4,5,6-tetrasubstituted piperidinones with four contiguous stereogenic centres.
Derivatives of phosphorous acid as a new class of ligands for Pd-catalyzed allylation
Moiseev,Lebedev,Polosukhin,Kalinin
, p. 554 - 556 (2001)
Amido- and aminophosphites and hydrospirophosphoranes can be used as ligands in the Pd-catalyzed allylation of ethyl malonate with ethyl (3-phenylprop-2-enyl) carbonate. Bidentate ligands (RO)2P - O(CH2)n - NR′2
Copper-catalyzed regiodivergent 1,4-and 1,6-conjugate silyl addition to diendioates: Access to functionalized allylsilanes
Ahmad, Tanveer,Li, Qi,Qiu, Sheng-Qi,Xu, Jian-Lin,Xu, Yun-He,Loh, Teck-Peng
, p. 6122 - 6126 (2019/07/03)
A copper-catalyzed regioselective 1,4-and 1,6-conjugate addition of a silyl reagent to diendioates was established. Various 1,4-and 1,6-protosilylation products were obtained in good yields and with high regioselectivity via tuning the ligands used in the reactions. This protocol has provided a simple and efficient method for the synthesis of multisubstituted functionalized allylsilanes.
Highly selective palladium-benzothiazole carbene-catalyzed allylation of active methylene compounds under neutral conditions
Monopoli, Antonio,Cotugno, Pietro,Zambonin, Carlo G.,Ciminale, Francesco,Nacci, Angelo
supporting information, p. 994 - 999 (2015/08/19)
The Pd-benzothiazol-2-ylidene complex I was found to be a chemoselective catalyst for the Tsuji-Trost allylation of active methylene compounds carried out under neutral conditions and using carbonates as allylating agents. The proposed protocol consists in a simplified procedure adopting an in situ prepared catalyst from Pd2dba3 and 3-methylbenzothiazolium salt V as precursors. A comparison of the performance of benzothiazole carbene with phosphanes and an analogous imidazolium carbene ligand is also proposed.
Metal-free, regio- and stereoselective synthesis of linear (E)-allylic compounds using C, N, O, and S nucleophiles
Huang, Xiaojun,Fulton, Brandon,White, Kana,Bugarin, Alejandro
, p. 2594 - 2597 (2015/06/16)
A variety of allylic acetates and derivatives were synthesized by an efficient two-step protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)- isomer as the sole adduct. This process tolerates several functional groups including halogen-containing molecules, and it is general for weak oxygen, carbon, nitrogen, and sulfur nucleophiles. Furthermore, adducts were obtained in good to excellent yields.
Metathesis transformations of unsaturated derivatives of β-diketones
Mi?tkiewski, Mi?osz,Powa?a, Beata,Staniszewski, Bartosz,Kubicki, MacIej,Urbaniak, W?odzimierz,Pietraszuk, Cezary
scheme or table, p. 728 - 736 (2012/04/17)
Selected β-diketones bearing unsaturated derivatives have been demonstrated to undergo homo-metathesis and cross-metathesis with selected olefins in the presence of Grubbs catalysts. The reactions led to respective homo- and cross-metathesis products mainly with good yields and selectivities. Versita Sp. z o.o.
A novel hemilabile calix[4],quinoline-based P,N-ligand: Coordination chemistry and complex characterisation
Marson, Angelica,Ernsting, Johanneke E.,Lutz, Martin,Spek, Anthony L.,Van Leeuwen, Piet W. N. M.,Kamer, Paul C. J.
experimental part, p. 621 - 633 (2009/05/06)
The synthesis of the calix[4]arene-based P,N-ligand 3 (5,11,17,23-tetra- tert-butyl-25-[(2-quinolylmethyl)oxy]-26,27,28-(μ3- phosphorustrioxy)calix[4]arene), in which the nitrogen atom-containing moiety has been introduced at the lower rim of t
Asymmetric three- and [2 + 1]-component conjugate addition reactions for the stereoselective synthesis of polysubstituted piperidinones
Davies, Stephen G.,Roberts, Paul M.,Smith, Andrew D.
, p. 1405 - 1415 (2008/02/10)
The efficiency and stereoselectivity of the conjugate addition of lithium (Z)- or (E)-β-amino ester enolates, generated by lithium amide conjugate addition to an α,β-unsaturated ester or deprotonation of a β-amino ester, respectively, to a range of α,β-unsaturated acceptors has been investigated. Deprotonation of a β-amino ester with LDA, followed by conjugate addition to a chiral α,β-unsaturated oxazolidinone gives high 2,3-anti selectivity (～90% d.e.), with hydrogenolysis and purification to homogeneity generating stereodefined trisubstituted piperidinones as single stereoisomers. Asymmetric three-component couplings of α,β-unsaturated esters and alkylidene malonates initiated by lithium amide conjugate addition proceeds with high levels of 2,3-anti stereoselectivity, with hydrogenolysis giving tetrasubstituted piperidinones. This journal is The Royal Society of Chemistry.
An improved catalytic system, Pd(PPh3)4/PhCOOH combined catalyst, for the allylation of carbon pronucleophiles with allenes
Patil, Nitin T.,Pahadi, Nirmal K.,Yamamoto, Yoshinori
, p. 2186 - 2190 (2007/10/03)
The reaction of allenes with active methynes and methylenes proceeded smoothly in the presence of Pd(PPh3)4/PhCOOH combined catalyst to give the corresponding monoallylated products with E-stereoselectivity in good to high yields. Th
